In 1994, while his peers were donning floor-length gowns and sleek tuxedos and dazzling the photographers, Jackson made no attempt to spiff up for the ACM Awards red carpet. Instead, he wore a pair of pants paired with a Hank Williams T-shirt -- and, to be honest, it looked more like a muscle shirt than a T-shirt. Jackson was, in effect, sticking it to the ACMs, and he explained his reasons backstage ... sort of.

"Well, I love Hank, and ... I get a lot of gifts on the road playing, and a fan gave me this shirt," Jackson said, "and I just saw it in the closet before I came out here this weekend, and I grabbed it and said, ‘I’m gonna wear it for my song,’ you know, "Gone Country." Hank’s country.”

When Jackson hopped on stage to perform at the ceremony, all eyes were on him and his Williams T-shirt. Soon, though, all eyes turned to his drummer, Bruce Rutherford, because although drum sounds were echoing throughout the venue, Rutherford had no drumsticks in hand. You see, before the show, ACM producers told Jackson to play along with a pre-recorded track -- a move that Jackson felt was dishonest to fans. So, he came up with the brilliant plan of having Rutherford play without drumsticks, to clue the audience in to what was going on.

Five years later, at the CMA Awards, Jackson was ticked off again. His friend George Jones was nominated for Single of the Year, for "Choices," but was only given one minute of stage time and told to play an abridged version of the song. Jones refused and stayed home, but Jackson cooked up another idea: He interrupted his own song "Pop a Top" to sing Jones' "Choices," much to the delight of the crowd. And so the story goes, Jones, who was watching from home, was moved to tears.

Press play on the video above to learn more about Jackson's outlaw decisions, rise to stardom and much more.